[SaaS Series] AI-Powered Employee Engagement Insights With Sanish Mondkar

Sanish Mondkar is the Founder and CEO of Legion Technologies, a company specializing in AI-powered workforce management solutions that optimize labor efficiency and enhance hourly employee engagement. Under his leadership, Legion has become a trusted platform for automating scheduling, forecasting, and communication across major industries. Before Legion, Sanish served as Executive Vice President and Chief Product Officer at SAP, and earlier at Ariba. He holds a bachelor’s degree in computer engineering from the University of Pune and a master’s in computer science from Cornell University.

Here’s a glimpse of what you’ll learn:

• [3:46] Sanish Mondkar explains how Legion is reinventing workforce management
• [8:00] The real reasons behind high hourly worker turnover
• [15:02] How Philz Coffee shaped Legion’s early product development and mission
• [18:03] Using AI-driven demand forecasting to optimize labor efficiency and scheduling
• [33:06] How instant pay transformed the hourly employee experience
• [37:14] The impact of generative AI on brick-and-mortar workforce operations
• [40:59] Overcoming adoption challenges and building trust in AI-powered automation
• [44:43] Legion’s growth milestones, from Philz Coffee to Dollar General
• [49:32] Sanish’s favorite resources on AI, health, and longevity

In this episode…

In today’s fast-paced world of retail, hospitality, and other hourly-based industries, companies are racing to balance efficiency with employee satisfaction. But as technology reshapes how businesses operate, can AI actually make hourly work more engaging, flexible, and fulfilling?

Sanish Mondkar, a seasoned technology leader and AI innovator, believes it can. He explains that traditional workforce management systems were built to control labor costs, not empower people — and that’s where AI can fundamentally shift the equation. By automating scheduling, predicting demand, and empowering employees with control over their work schedules, companies can reduce attrition while fostering a more motivated workforce. Sanish also points out that real transformation comes when AI is transparent, explainable, and trusted by both managers and frontline workers.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Sanish Mondkar, Founder and CEO of Legion Technologies, to discuss how AI can drive employee engagement and operational excellence. They talk about Legion’s AI-powered scheduling innovations, the “trifecta” that reduces attrition, and how automation builds trust between employers and staff. Sanish also shares lessons from scaling Legion with major brands like Dollar General and Philz Coffee.

Resources mentioned in this episode:

• Sanish Mondkar on LinkedIn
• Legion Technologies
• Drive: The Surprising Truth About What Motivates Us by Daniel H. Pink
• Philz Coffee
• State of the Hourly Workforce | HR Executive Summary
• Dwarkesh Podcast
• David Sinclair
• Young Forever: The Secrets to Living Your Longest, Healthiest Life by Dr. Mark Hyman, MD
• Outlive: The Science and Art of Longevity by Peter Attia, MD and Bill Gifford
• Peter Attia

Special mentions:

• Jacob Jaber on LinkedIn
• Maynard Webb on LinkedIn
• Webb Investment Network Labs
• Ross Fubini on LinkedIn
• XYZ Venture Capital
• Norwest Venture Partners
• Gopal Sundaram on LinkedIn

Related episodes:

• “Automation Solutions with Wade Foster Founder of Zapier” on the Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on the Inspired Insider Podcast
• “[SaaS Series] Tips To Thrive in the SaaS Space With Sujan Patel” on the Inspired Insider Podcast
• “[SaaS Series] Revolutionizing Online Forms and Productivity With Aytekin Tank of Jotform” on the Inspired Insider Podcast

Quotable moments:

• “Workforce management should be more holistic and inclusive. It should provide value to employers and employees.”
• “We call it schedule ownership at Legion — owning the schedule is probably the most important thing.”
• “Our data shows you will cut your attrition by roughly 35%, which is massive.”
• “If you’re going to solve frontline worker experience problems, you better step into their shoes.”
• “Explainability and transparency build trust — that’s what drives adoption of AI-powered automation in the workplace.”

Action steps:

1. Empower employees with schedule ownership: Give workers control over their schedules to reduce turnover and support better work-life balance.
2. Modernize employee experience through technology: Use mobile-first tools to streamline communication and create a workplace experience that meets modern expectations.
3. Offer on-demand pay options: Allow employees to access earned wages immediately to increase satisfaction and reduce attrition.
4. Use AI-driven demand forecasting and scheduling: Apply AI to match labor needs with employee preferences for greater efficiency and fairness.
5. Prioritize transparency and explainability in automation: Ensure automated scheduling decisions are clear and understandable to build trust and encourage adoption.

Episode Transcript

Intro: 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz: 00:22

Dr. Jeremy Weisz here, Founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Sanish Mondkar. You can check him out at Legion.co. And Sanish, before I formally introduce you, I always like to point out other episodes of the podcast people should check out.

Since this is part of our top SaaS and AI series, you know, if you go to Legion, you go to Legion AI, they have a little, you know, in the navigation there and check out what they’re doing. He’s got a lot of thoughts on AI. And, you know, you have a unique perspective on this because you help a lot of not just, you know, tech companies like brick and mortar, you know, in various industries. So we’re going to dig into that.

Some other episodes of the podcast in that genre. I had the co-founder of Zapier on. That was a really good episode, one of the co-founders of Pipedrive, a great episode there. Mailshake, also, he talked about how he has been acquiring SaaS companies. So and the founder of Jotform as well, and what they’re doing and how he grew to 25 million users. It was pretty incredible. So that and many more and InspiredInsider.com.

This episode is brought to you by Rise25. At Rise25, we help businesses connect to their dream relationships and partnerships. We do that in a few ways. One, we’re an easy button for a company to launch and run a podcast so they get ROI. We do the strategy, accountability, and the full execution and production. Number two, we’re an easy button for a company’s gifting, so we make gifting, staying top of mind. Could be for clients, for partners, for prospects, for even staff from a culture perspective. Simple, easy and actually affordable. You just give. Give us a list of the people.

We do everything of the sending. It’s all branded to your company, by the way. We don’t. Send like tchotchkes. Not there’s anything wrong with that. But we like sending food. Actually, because I like getting food, Sanish. So the number one thing, we call ourselves kind of the magic elves that run in the background to make it stress free for a company to build amazing relationships. And that’s the number one thing in my life, is relationships.

And I always look at ways how I can give to my best relationships. And I found no better way. Over the past 15 years than to profile the people and companies I admire and send them sweet treats in the mail so you can check it out at Rise25.com, or email [email protected].

I’m really excited to introduce Sanish Mondkar. He’s the CEO and Founder of Legion.Co, and he has more than 20 years of strategic experience in products and technology. He had a previous role as Chief Product Officer at SAP, and he was responsible for all procurement and business network products and technology. Just to give you an idea of the realm of that, it represented over $1 billion of annual revenue. So no small feat there. It’s a big position. Parlayed those skills and leadership into starting Legion, and Legion is reinventing the way businesses can manage and engage with their hourly workforce.

They use data driven and AI based approach that basically upgrades the operational efficiency for the employer side, and also the job satisfaction for the employees. So thanks for joining me.

Sanish Mondkar: 03:40

Thank you. Thanks for having me.

Dr. Jeremy Weisz: 03:42

So let’s start off, just talk about Legion and what you do. I’m going to pull up the website.

Sanish Mondkar: 03:46

Yeah. So as you mentioned Legion is reinventing workforce management as a category. So workforce management is an enterprise category, enterprise software category that’s been around for a while. Its genesis was in accurately managing hourly workforce, especially from a payroll accuracy standpoint. As you know, there are many, many labor intensive industries out there: retail, hospitality, manufacturing, distribution centers, so on and so forth.

In fact, hourly workforce represents a majority of the workforce in the United States and in the world. So there were these platforms built historically, which would be focused on managing employees timesheets and making sure they’re clocking in properly and.

Dr. Jeremy Weisz: 04:35

It’s a pain in the butt.

Sanish Mondkar: 04:36

Yeah. And making sure that they’re getting paid accurately. And those evolved to become workforce management platforms where the next problem they start solving was scheduling employees, you know, to the point of demand and shift management and so on and so forth. Where Legion came in was when we looked at what was built for decades prior to us. We said, as great as solving some real problems is a very important category of software for labor intensive businesses.

But there were two things missing and they were really, really foundational things. First is workforce management wasn’t really automated. It wasn’t a high tech category. There was a lot of efficiency that you could gain by just automating it smartly, like we call it intelligent automation at Legion. But more importantly, workforce management was not built to deliver any value to the workforce.

It was built with the cost management and labor optimization or wage optimization. Pick any of these terms. It was really meant to protect employers from excessive cost of labor, which is an important goal, don’t get me wrong. But employees for most of these industries, the workforce management platform is probably the only platform employees touch on a regular basis. So in other words, that platform had the opportunity to add value to the employee with every single engagement and interaction.

But it kind of completely missed that opportunity. And instead it just focused on cost and efficiency and things like that. We thought that was an incomplete platform. When I founded Legion, I said, look, workforce management should be more holistic and inclusive. It should provide value to the employer and the employees.

In fact, if an employer does a better job of engaging and adding value to the employees experience, the employee turnover would be much lower, which, as you know, in these industries is really very, very high. And you would actually end up saving more on cost of labor by reducing your cost of worker replacement. So the whole picture of how workforce management should evolve partly or fully automated and employee centric is what made sense to us. And that’s why that’s why the company was founded. Now I’ll say one more thing.

As we started digging into what we need to do, we realized very quickly we had to reinvent and rebuild workforce management from the ground up to really make this possible. And that’s what we’ve been working on for nine years. We’ve been very successful in taking our brand of workforce management to the market. And as you see in our website, a lot of capabilities and a lot of great customers who have chosen us.

Dr. Jeremy Weisz: 07:28

You know, I have a lot of questions on that, and I’ll get into why even start this type of company in the first place. But I want to get into one thing you said before we get to that, which is, you know, obviously the employer side, it makes sense, right? It helps keep track of hourly employees. It helps manage a bunch of schedules. What have you found?

How did you get the employees liking it and, you know, increasing their job satisfaction. What features in the platform did you build in for that purpose?

Sanish Mondkar: 08:00

Yeah. So when you think about, so let’s say let’s take food and beverage industry, especially QSR, the turnover rate of employees is in most cities over 100%. Right. Which is kind of insane when you think about it. Like for our jobs, imagine you lose all your colleagues.

Dr. Jeremy Weisz: 08:17

It’s terrible. Yeah. I’m looking at your website, some of my favorites. You have Portillo’s on there love. Portillo’s you have Panda Express on there. A bunch of quick service. Yeah.

Sanish Mondkar: 08:28

And retail is close to 75% you know US turnover. So these are very very high numbers right now. But here’s the real insight. When you dig in and you dig in data and you look at a lot of these, you look at employee feedback. We at Legion, almost since the founding days, we do an annual survey of hourly workers and managers.

We’ve done a lot of research on both from our customers but also from the market. And here’s the unique insight. The unique insight is actually employees are not leaving because of pay. And once you understand that, you’re like, well, what are they? Oh my God, what are they leaving for?

Right. And the reason why we know they’re not leaving for pay is because pay tends to be standardized across these jobs in a metropolitan area or a city or a state and things like that. Right. So, for example, a restaurant worker in San Francisco where I live is not going to likely find another restaurant across the street that pays more, right? But at the same time, they’re leaving out over 100% turnover rates.

So what? So what is it? It’s worth asking that question because every worker that you can prevent leaving or prevent the attrition is actually going to be a happier worker who is going to serve your customers better. You are not incurring a cost of worker replacement, which is hiring and training costs and all those things. So it’s worth asking this question.

And we obsessed with that question especially in the early days of Legion. And we found out initially there were two things. Now there is a third thing that has emerged, right? So now today I call that as the trifecta of employee engagement for hourly workers. And if you do those three things you don’t have, you know, if you can do it without Legion, more power to you.

But the more important thing is do it. And those three things are enabling employees to own their schedule to whatever extent is possible and feasible for your business. Right? Sometimes 100% ownership, like a gig job, is not possible. But to the extent it’s possible because most of the friction with the job comes from I can’t work this Thursday, but next week I want to work Thursday or maximize.

I’m balancing this job with two other jobs or school or all the, so the friction.

Dr. Jeremy Weisz: 10:49

Giving people flexibility.

Sanish Mondkar: 10:51

Exactly. We call it schedule ownership at leisure. Owning the schedule and schedule ownership is not just about time and day, but also I want more hours. I want less hours because hours directly translates to pay. So that is probably the most important thing you can do.

Following that is giving a reasonable experience to your employees in terms of, you know, like today, close to 25% of the workforce in these industries is Gen Z. Over 60% are millennials. I mean, these are internet generations. They’re not coming to these jobs. And they don’t get any company email addresses.

Nine out of ten retailers don’t have anything of that sort. So just the experience of do I have to negotiate everything with my managers? Can I just go to an app and make the, you know, inputs a few things and get at least some things done. Is it efficient? Is it?v Is it modern? Is it digital? Is there a mobile app? Those things really matter, right? And they did not matter ten years ago as much to the extent that they do now.

But now it’s really employees have choices. They can get that type of flexibility and experience by doing DoorDash jobs or other jobs instead of a retail or a QSR jobs. The pay is going to be the same. So that’s what you’re competing with as a brick and mortar business, and you need to up your game of employee experience. And more important and equally important, the third leg of that stool, which has emerged in the past 2 to 3 years, is what we call earned wage access.

After my shift is over, I need to get paid. Why am I waiting for a week for your payroll to run, or two weeks for your payroll to run? That’s what gig jobs give you. I would expect that in my retail jobs and my brick and mortar jobs, in my distribution center jobs and my manufacturing jobs. So if you do those three things schedule ownership, a modern experience for communications and self-service and earned wage access, instant pay as it’s called you.

Our data shows you will cut your term, your attrition by roughly 35%, which is massive.

Dr. Jeremy Weisz: 13:06

Can you talk about the platform in those three things for a second? So with Legion, you said own your own schedule. By the way, there’s a great book, Drive by Daniel Pink. It talks about kind of this, some of the research behind what you’re talking about and giving people autonomy does allow people to kind of swap with their other staff members easily and kind of communicate.

Sanish Mondkar: 13:31

Absolutely. And the thing about doing that properly is swapping is, you know, swapping shifts could be done in a way that creates some business risk, like there could be compliance risk and things like that. But swapping can also be done in a way that those things are taken care of by the platform. Right? So that’s what I mean by true self-service.

Whether the employer is actually not suffering any type of consequences of the self-service and empowerment that’s provided to the employees. And there are many, many examples of this. Swapping is probably one of the easiest ones, but there are like 100 other things that the platform does.

Dr. Jeremy Weisz: 14:10

But yeah, I mean, I’m just saying, like I could visualize people, what normally happens is they okay, they try and get their coworkers numbers. They’re texting different people trying to find answers. Right.

And I could see this really paramount in healthcare. Right? I know you help healthcare because I’m a nurse or, you know, someone like that that listen, I gotta do something. I need to have someone replace me. There’s probably pre-approvals that are in place that allow people to kind of to do that very easily.

I’m curious the evolution of the type of customers you work with, right? Because, you know, there’s you know, I know you have convenience stores. You have health and fitness, you have healthcare, hospitality, pet care. You talked about restaurants. Where did it start? And then, you know, you could have probably just focused forever on restaurants and been busy.

Sanish Mondkar: 15:02

It started with quick serve restaurants, specifically cafes in the San Francisco Bay area, in particular Philz Coffee. So I’m a huge fan of Philz Coffee and they were our first customers. They were very forward looking about, you know, really enabling and empowering their baristas to be more autonomous in terms of creating the schedules and picking their shifts and things like that. But they wanted to make sure that the overall labor efficiency and cost is also taken care of and under control. So which meant that you have to solve both sides of the equation.

It’s one thing to provide autonomy to employees and things like that. But you also have to guarantee that it doesn’t come with a greater cost to the customer. Right. To the employer. So we built a lot of early capabilities where and one of those capabilities is demand forecasting, which is still completely powered.

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